FI56965C - Foerfarande foer framstaellning av d d-penicillamin - Google Patents

Foerfarande foer framstaellning av d d-penicillamin Download PDF

Info

Publication number: FI56965C
Authority: FI; Finland
Prior art keywords: acid; norephedrine; penicillamine; mol; formylisopropylidene
Prior art date: 1972-11-29

Application number

FI3151/73A

Other languages

English (en)

Finnish (fi)

Other versions

FI56965B (fi

Inventor

Friedrich Asinger

Heribert Offermanns

Karl-Heinz Gluzek

Walter Von Bebenburg

Original Assignee

Degussa

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.)

1972-11-29

Filing date

1973-10-11

Publication date

1980-05-12

1973-10-11 Application filed by Degussa filed Critical Degussa

1980-01-31 Publication of FI56965B publication Critical patent/FI56965B/fi

1980-05-12 Application granted granted Critical

1980-05-12 Publication of FI56965C publication Critical patent/FI56965C/fi

Links

VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical compound CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 title claims description 6
DLNKOYKMWOXYQA-CBAPKCEASA-N (-)-norephedrine Chemical compound C[C@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-CBAPKCEASA-N 0.000 claims description 25
238000000034 method Methods 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
229960001639 penicillamine Drugs 0.000 claims description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
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 3
235000011054 acetic acid Nutrition 0.000 claims description 3
150000001735 carboxylic acids Chemical class 0.000 claims description 3
235000019253 formic acid Nutrition 0.000 claims description 3
VVNCNSJFMMFHPL-UHFFFAOYSA-N penicillamine Chemical compound CC(C)(S)C(N)C(O)=O VVNCNSJFMMFHPL-UHFFFAOYSA-N 0.000 claims description 3
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
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000011833 salt mixture Substances 0.000 claims 1
239000000047 product Substances 0.000 description 14
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
230000008878 coupling Effects 0.000 description 8
238000010168 coupling process Methods 0.000 description 8
238000005859 coupling reaction Methods 0.000 description 8
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 5
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
-1 aliphatic sulfonic acids Chemical class 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
235000013985 cinnamic acid Nutrition 0.000 description 3
229930016911 cinnamic acid Natural products 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
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-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
150000007513 acids Chemical class 0.000 description 2
229940077388 benzenesulfonate Drugs 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-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
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
DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 description 2
229960000395 phenylpropanolamine Drugs 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
230000007017 scission Effects 0.000 description 2
150000003460 sulfonic acids Chemical class 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
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
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
239000005711 Benzoic acid Substances 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
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
VVNCNSJFMMFHPL-GSVOUGTGSA-N L-penicillamine Chemical compound CC(C)(S)[C@H](N)C(O)=O VVNCNSJFMMFHPL-GSVOUGTGSA-N 0.000 description 1
125000003047 N-acetyl group Chemical group 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
125000001931 aliphatic group Chemical group 0.000 description 1
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 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
125000004432 carbon atom Chemical group C* 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
230000004927 fusion Effects 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000001072 heteroaryl 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
230000000116 mitigating effect Effects 0.000 description 1
239000000203 mixture Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids 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
239000002244 precipitate Substances 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
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 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)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Medicines Containing Plant Substances (AREA)

FI3151/73A 1972-11-29 1973-10-11 Foerfarande foer framstaellning av d d-penicillamin FI56965C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE2258411A DE2258411C3 (de)	1972-11-29	1972-11-29	Verfahren zur Gewinnung von D-Penicillamin
DE2258411		1972-11-29

Publications (2)

Publication Number	Publication Date
FI56965B FI56965B (fi)	1980-01-31
FI56965C true FI56965C (fi)	1980-05-12

Family

ID=5863013

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI3151/73A FI56965C (fi)	1972-11-29	1973-10-11	Foerfarande foer framstaellning av d d-penicillamin

Country Status (24)

Country	Link
JP (1)	JPS5512423B2 (da)
AR (1)	AR203731A1 (da)
BE (1)	BE806378R (da)
BR (1)	BR7309342D0 (da)
CA (1)	CA1003853A (da)
CH (1)	CH590182A5 (da)
CS (1)	CS183693B2 (da)
DD (1)	DD109215A6 (da)
DE (1)	DE2258411C3 (da)
DK (1)	DK146414C (da)
ES (1)	ES418693A2 (da)
FI (1)	FI56965C (da)
FR (1)	FR2207886B2 (da)
GB (1)	GB1413038A (da)
HU (1)	HU168379B (da)
IE (1)	IE38489B1 (da)
IL (1)	IL43567A (da)
IT (1)	IT1045950B (da)
NL (1)	NL163786C (da)
NO (1)	NO138948C (da)
RO (1)	RO71923A7 (da)
SE (1)	SE382048B (da)
SU (1)	SU535900A4 (da)
ZA (1)	ZA738498B (da)

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 JP JP13297873A patent/JPS5512423B2/ja not_active Expired
- 1973-11-27 DK DK638973A patent/DK146414C/da not_active IP Right Cessation
- 1973-11-27 FR FR7342210A patent/FR2207886B2/fr not_active Expired
- 1973-11-28 RO RO7376809A patent/RO71923A7/ro unknown
- 1973-11-28 CS CS7300008188A patent/CS183693B2/cs unknown
- 1973-11-28 SU SU1973450A patent/SU535900A4/ru active
- 1973-11-28 SE SE7316110A patent/SE382048B/xx unknown
- 1973-11-28 BR BR9342/73A patent/BR7309342D0/pt unknown
- 1973-11-29 NL NL7316344.A patent/NL163786C/xx not_active IP Right Cessation
- 1973-11-29 CA CA186,936A patent/CA1003853A/en not_active Expired

Also Published As

Publication number	Publication date
CH590182A5 (da)	1977-07-29
JPS5512423B2 (da)	1980-04-02
ES418693A2 (es)	1977-11-01
FI56965B (fi)	1980-01-31
BR7309342D0 (pt)	1974-08-29
FR2207886A2 (da)	1974-06-21
HU168379B (da)	1976-04-28
NL7316344A (da)	1974-05-31
SE382048B (sv)	1976-01-12
FR2207886B2 (da)	1978-01-06
IT1045950B (it)	1980-06-10
SU535900A4 (ru)	1976-11-15
IE38489L (en)	1974-05-29
BE806378R (fr)	1974-02-15
AU6244773A (en)	1975-05-15
AR203731A1 (es)	1975-10-15
NL163786C (nl)	1980-10-15
CS183693B2 (en)	1978-07-31
ZA738498B (en)	1974-10-30
JPS4982627A (da)	1974-08-08
NL163786B (nl)	1980-05-16
DD109215A6 (da)	1974-10-20
GB1413038A (en)	1975-11-05
DK146414C (da)	1984-03-12
DE2258411C3 (de)	1981-01-22
CA1003853A (en)	1977-01-18
NO138948C (no)	1978-12-13
IE38489B1 (en)	1978-03-29
DE2258411A1 (de)	1974-06-06
DK146414B (da)	1983-10-03
IL43567A (en)	1976-04-30
RO71923A7 (ro)	1981-07-30
NO138948B (no)	1978-09-04
DE2258411B2 (de)	1980-01-24

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