CH635347A5 - Stable solutions of hydrogenated ergot alkaloids or their synthetic derivatives in a mixture of alcohols and water - Google Patents

Stable solutions of hydrogenated ergot alkaloids or their synthetic derivatives in a mixture of alcohols and water Download PDF

Info

Publication number: CH635347A5
Authority: CH; Switzerland
Prior art keywords: mixture; water; weight; stable solutions; alcohols
Prior art date: 1977-08-06

Application number

CH796478A

Other languages

German (de)

English (en)

Inventor

Lothar Dr Ehrhardt

Ludwig Dr Patt

Volker Dr Hartmann

Original Assignee

Sandoz Ag

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.)

1977-08-06

Filing date

1978-07-24

Publication date

1983-03-31

1978-07-24 Application filed by Sandoz Ag filed Critical Sandoz Ag

1983-03-31 Publication of CH635347A5 publication Critical patent/CH635347A5/de

Links

239000000203 mixture Substances 0.000 title claims description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 24
150000001298 alcohols Chemical class 0.000 title claims description 8
PBKVEOSEPXMKDN-LZHUFOCISA-N chembl2311030 Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)C)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)CC)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)CC(C)C)C(C)C)=C3C2=CNC3=C1.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C(C)C)C1=CC=CC=C1 PBKVEOSEPXMKDN-LZHUFOCISA-N 0.000 title claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
238000000034 method Methods 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
239000000243 solution Substances 0.000 description 26
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
239000011877 solvent mixture Substances 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
150000005846 sugar alcohols Polymers 0.000 description 8
150000001875 compounds Chemical class 0.000 description 6
235000011187 glycerol Nutrition 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
QHZUABXEBRGBLP-LKWYKXIFSA-N (6aR,9R,10aR)-N-[(2R,4R,9aS,9bR)-4-benzyl-9b-hydroxy-3,5-dioxo-2-propan-2-yl-3a,4,7,8,9,9a-hexahydrofuro[3,2-g]indolizin-2-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide (6aR,9R,10aR)-N-[(2R,4R,9aS,9bR)-9b-hydroxy-3,5-dioxo-2,4-di(propan-2-yl)-3a,4,7,8,9,9a-hexahydrofuro[3,2-g]indolizin-2-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide (6aR,10aR)-N-[(2S,4S,9bS)-9b-hydroxy-4-(2-methylpropyl)-3,5-dioxo-2-propan-2-yl-3a,4,7,8,9,9a-hexahydrofuro[3,2-g]indolizin-2-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)C4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)C)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2CC(CN(C)[C@@H]2C2)C(=O)N[C@@]3(C(=O)C4[C@@H](C(N5CCCC5[C@@]4(O)O3)=O)CC(C)C)C(C)C)=C3C2=CNC3=C1.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(C21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C(C)C)C1=CC=CC=C1 QHZUABXEBRGBLP-LKWYKXIFSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 3
229960004318 dihydroergocristine Drugs 0.000 description 3
HESHRHUZIWVEAJ-JGRZULCMSA-N dihydroergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C)C1=CC=CC=C1 HESHRHUZIWVEAJ-JGRZULCMSA-N 0.000 description 3
229960004704 dihydroergotamine Drugs 0.000 description 3
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
239000011261 inert gas Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
229960000541 cetyl alcohol Drugs 0.000 description 2
LIMAOLZSWRJOMG-HJPBWRTMSA-N dihydroergocristine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C(C)C)C1=CC=CC=C1 LIMAOLZSWRJOMG-HJPBWRTMSA-N 0.000 description 2
ADYPXRFPBQGGAH-UMYZUSPBSA-N dihydroergotamine mesylate Chemical compound CS(O)(=O)=O.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C)C1=CC=CC=C1 ADYPXRFPBQGGAH-UMYZUSPBSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 2
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 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
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 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
239000003990 capacitor Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
DEQITUUQPICUMR-HJPBWRTMSA-N dihydroergocristine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C(C)C)C1=CC=CC=C1 DEQITUUQPICUMR-HJPBWRTMSA-N 0.000 description 1
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000007654 immersion Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
238000000691 measurement method Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
235000021313 oleic acid Nutrition 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
238000011085 pressure filtration Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 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

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/48—Ergoline derivatives, e.g. lysergic acid, ergotamine

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)

CH796478A 1977-08-06 1978-07-24 Stable solutions of hydrogenated ergot alkaloids or their synthetic derivatives in a mixture of alcohols and water CH635347A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772735587 DE2735587A1 (de)	1977-08-06	1977-08-06	Stabile loesungen und verfahren zu deren herstellung

Publications (1)

Publication Number	Publication Date
CH635347A5 true CH635347A5 (en)	1983-03-31

Family

ID=6015843

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH796478A CH635347A5 (en)	1977-08-06	1978-07-24	Stable solutions of hydrogenated ergot alkaloids or their synthetic derivatives in a mixture of alcohols and water

Country Status (23)

Country	Link
JP (1)	JPS5428811A (cs)
AT (1)	AT364463B (cs)
AU (1)	AU525725B2 (cs)
BE (1)	BE869560R (cs)
CA (1)	CA1111348A (cs)
CH (1)	CH635347A5 (cs)
CS (1)	CS203199B2 (cs)
DE (1)	DE2735587A1 (cs)
DK (1)	DK337678A (cs)
FI (1)	FI782341A7 (cs)
FR (1)	FR2399248A2 (cs)
GB (1)	GB1596948A (cs)
GR (1)	GR72791B (cs)
IE (1)	IE47791B1 (cs)
IL (1)	IL55285A (cs)
IT (1)	IT1202759B (cs)
NL (1)	NL7808122A (cs)
NO (1)	NO147901C (cs)
NZ (1)	NZ188073A (cs)
PT (1)	PT68386A (cs)
SE (1)	SE444114B (cs)
YU (1)	YU188378A (cs)
ZA (1)	ZA784435B (cs)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2930369A1 (de) *	1979-07-26	1981-02-05	Rentschler Arzneimittel	Arzneimittelloesungen
DE2945636A1 (de) *	1979-11-12	1981-05-21	Sandoz-Patent-GmbH, 7850 Lörrach	Stabile loesungen von hydrierten ergotalkaloiden bzw. ihren salzen und heparin bzw. seinen salzen sowie verfahren zu deren herstellung
DE3227122A1 (de) *	1982-07-20	1984-01-26	Dr. Rentschler Arzneimittel Gmbh & Co, 7958 Laupheim	Stabile loesungen von mutterkornalkaloiden
IT1200609B (it) *	1985-04-04	1989-01-27	Poli Ind Chimica Spa	Composizione farmaceutice per il trattamento delle turbe cerebrovascolari e del cervello anziano
AT381232B (de) *	1985-05-13	1986-09-10	Kwizda Fa F Johann	Verfahren zur herstellung stabiler fluessiger loesungen von ergolinderivaten
GB8629781D0 (en) *	1986-12-12	1987-01-21	Glaxo Group Ltd	Pharmaceutical compositions
WO2000057851A2 (en) *	1999-03-26	2000-10-05	Pozen Inc.	High potency dihydroergotamine compositions
DE102007014947B4 (de)	2007-03-23	2010-05-27	Axxonis Pharma Ag	Stabilisierte wässrige Lösungen von Ergolinverbindungen

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3749779A (en) *	1970-08-27	1973-07-31	American Home Prod	Stable solutions of sodium diphenylhydantoin

1977
- 1977-08-06 DE DE19772735587 patent/DE2735587A1/de not_active Withdrawn
1978
- 1978-05-30 GB GB23758/78A patent/GB1596948A/en not_active Expired
- 1978-07-24 CH CH796478A patent/CH635347A5/de not_active IP Right Cessation
- 1978-07-27 FI FI782341A patent/FI782341A7/fi not_active Application Discontinuation
- 1978-07-28 SE SE7808210A patent/SE444114B/sv unknown
- 1978-07-28 DK DK337678A patent/DK337678A/da not_active Application Discontinuation
- 1978-07-28 NO NO782605A patent/NO147901C/no unknown
- 1978-08-02 IT IT26407/78A patent/IT1202759B/it active
- 1978-08-02 NL NL787808122A patent/NL7808122A/xx not_active Application Discontinuation
- 1978-08-03 YU YU01883/78A patent/YU188378A/xx unknown
- 1978-08-04 CA CA308,775A patent/CA1111348A/en not_active Expired
- 1978-08-04 PT PT68386A patent/PT68386A/pt unknown
- 1978-08-04 BE BE78189738A patent/BE869560R/xx not_active IP Right Cessation
- 1978-08-04 IE IE1598/78A patent/IE47791B1/en unknown
- 1978-08-04 FR FR7823160A patent/FR2399248A2/fr active Granted
- 1978-08-04 NZ NZ188073A patent/NZ188073A/xx unknown
- 1978-08-04 IL IL55285A patent/IL55285A/xx unknown
- 1978-08-04 AU AU38676/78A patent/AU525725B2/en not_active Expired
- 1978-08-04 AT AT0567378A patent/AT364463B/de not_active IP Right Cessation
- 1978-08-04 CS CS785139A patent/CS203199B2/cs unknown
- 1978-08-04 GR GR56936A patent/GR72791B/el unknown
- 1978-08-04 ZA ZA784435A patent/ZA784435B/xx unknown
- 1978-08-05 JP JP9576378A patent/JPS5428811A/ja active Pending

Also Published As

Publication number	Publication date
FR2399248A2 (fr)	1979-03-02
SE444114B (sv)	1986-03-24
IE47791B1 (en)	1984-06-27
FI782341A7 (fi)	1979-02-07
IL55285A (en)	1981-09-13
IT7826407A0 (it)	1978-08-02
IL55285A0 (en)	1978-10-31
ZA784435B (en)	1980-03-26
CA1111348A (en)	1981-10-27
ATA567378A (de)	1981-03-15
BE869560R (fr)	1979-02-05
IE781598L (en)	1979-02-06
AT364463B (de)	1981-10-27
JPS5428811A (en)	1979-03-03
DE2735587A1 (de)	1979-02-15
AU525725B2 (en)	1982-11-25
GR72791B (cs)	1983-12-05
NO147901B (no)	1983-03-28
FR2399248B2 (cs)	1980-07-18
NZ188073A (en)	1980-12-19
IT1202759B (it)	1989-02-09
PT68386A (en)	1978-09-01
GB1596948A (en)	1981-09-03
NO147901C (no)	1983-07-06
DK337678A (da)	1979-02-07
NL7808122A (nl)	1979-02-08
CS203199B2 (en)	1981-02-27
SE7808210L (sv)	1979-02-07
YU188378A (en)	1984-02-29
AU3867678A (en)	1980-02-07
NO782605L (no)	1979-02-07

Legal Events

Date	Code	Title	Description
1997-05-15	PFA	Name/firm changed	Owner name: SANDOZ AG TRANSFER- NOVARTIS AG
1998-08-14	PL	Patent ceased

Publication	Publication Date	Title
DE3040208C2 (de)	1982-10-14	Suppositoriengrundlage
CH667203A5 (de)	1988-09-30	Dihydropyridinspray und verfahren zu seiner herstellung.
DE1670616B2 (de)	1977-11-10	14-hydroxydihydronormorphinverbindungen und verfahren zu ihrer herstellung
DE1493856B2 (de)	1977-03-17	1-aryloxy-3-(n-alkylamino)-2-propanole, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische mittel
DE3429415A1 (de)	1986-01-02	Wasserfreie, stabile und kristalline form von prazosinhydrochlorid und verfahren zu dessen herstellung
DE60104398T2 (de)	2004-11-25	Verfahren zur herstellung von triethanolamin und nach dem verfahren erhaltenes produkt
CH635347A5 (en)	1983-03-31	Stable solutions of hydrogenated ergot alkaloids or their synthetic derivatives in a mixture of alcohols and water
DE2062001C2 (de)	1986-10-16	1,2,3,4-Tetrahydro-4-phenylisochinolin-Derivate, deren Säureadditionssalze, Verfahren zu deren Herstellung und pharmazeutisches Präparat
DE2257715A1 (de)	1973-05-30	6-methylen-6-desoxydihydromorphinund codeinderivate
DE3131950A1 (de)	1982-03-25	Metalldesaktivator und diesen enthaltende zusammensetzung
DE2432680A1 (de)	1975-01-30	Verfahren zur herstellung von polyestern und ihre verwendung in schmieroelen
CH618684A5 (cs)	1980-08-15
DE3620218A1 (de)	1987-01-02	Verfahren zur herstellung von 1,2-substituierten imidazolin-verbindungen
DE2246307C2 (de)	1982-11-04	In 1 Stellung substituierte 3-Hydroxymethyl-6,7-dialkoxy-isochinoline, deren Salze und Verfahren zur ihrer Herstellung
AT402690B (de)	1997-07-25	Sprühbare lösungen mit blutdrucksenkender wirkung und verfahren zu ihrer herstellung sowie ihre verwendung
DE1906038C3 (de)	1973-11-08	Schmiermittel
DE2555481C3 (de)	1985-10-03	Herstellung stabiler Tropflösungen von hydrierten Ergotalkaloiden
DE2323192A1 (de)	1973-12-13	Injizierbare, langwirkende antagonistpraeparate gegen narkotika und rauschgifte
DE1595889B2 (de)	1973-10-18	Imidazo eckige Klammer auf 1,2-a eckige Klammer zu pyridine und ein Verfahren zu ihrer Herstellung. Ausscheidung aus: 1426904
EP0237946A1 (de)	1987-09-23	Kupferhaltiges Mittel zur Bekämpfung von Pilzen und Bakterien
DE1811478C3 (de)	1978-04-06	Hydroxylierte Verbindungen, deren Herstellung und diese enthaltende Mittel
DE1090215B (de)	1960-10-06	Verfahren zur Herstellung von Phenthiazinderivaten
DE3434593C2 (cs)	1988-11-24
DE2200600A1 (de)	1972-08-10	Verfahren zum Herstellen von Pyrrolidonen
DE835927C (de)	1952-04-07	Verfahren zur Herstellung von bestaendigen waessrigen Loesungen des Theophyllins