JPS5943463B2 - ジベンゾピラノンの多形結晶型化合物の製法 - Google Patents
ジベンゾピラノンの多形結晶型化合物の製法Info
- Publication number
- JPS5943463B2 JPS5943463B2 JP49127923A JP12792374A JPS5943463B2 JP S5943463 B2 JPS5943463 B2 JP S5943463B2 JP 49127923 A JP49127923 A JP 49127923A JP 12792374 A JP12792374 A JP 12792374A JP S5943463 B2 JPS5943463 B2 JP S5943463B2
- Authority
- JP
- Japan
- Prior art keywords
- crystalline compound
- dimethyl
- hydroxy
- polymorphic crystalline
- hexahydro
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- SEQIMZPSZATKQD-UHFFFAOYSA-N benzo[c]chromen-9-one Chemical compound C1=CC=C2C3=CC(=O)C=CC3=COC2=C1 SEQIMZPSZATKQD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 238000004455 differential thermal analysis Methods 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 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 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicinal Preparation (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41301173A | 1973-11-05 | 1973-11-05 | |
| US413011 | 1973-11-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5082222A JPS5082222A (da) | 1975-07-03 |
| JPS5943463B2 true JPS5943463B2 (ja) | 1984-10-22 |
Family
ID=23635422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49127923A Expired JPS5943463B2 (ja) | 1973-11-05 | 1974-11-05 | ジベンゾピラノンの多形結晶型化合物の製法 |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5943463B2 (da) |
| AR (1) | AR202670A1 (da) |
| AT (1) | AT335453B (da) |
| BE (1) | BE821720A (da) |
| BG (1) | BG27088A3 (da) |
| CA (1) | CA1028715A (da) |
| CS (1) | CS174793B2 (da) |
| DD (1) | DD115660A5 (da) |
| DE (1) | DE2449927C2 (da) |
| DK (1) | DK136720B (da) |
| ES (1) | ES431672A1 (da) |
| FR (1) | FR2249665B1 (da) |
| GB (1) | GB1487635A (da) |
| HU (1) | HU167751B (da) |
| IE (1) | IE39678B1 (da) |
| IL (1) | IL45742A (da) |
| NL (1) | NL7412682A (da) |
| PH (1) | PH11719A (da) |
| PL (1) | PL94119B1 (da) |
| RO (1) | RO71769A (da) |
| SE (1) | SE407062B (da) |
| SU (1) | SU611591A3 (da) |
| YU (1) | YU287874A (da) |
| ZA (1) | ZA746029B (da) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4278603A (en) * | 1973-11-05 | 1981-07-14 | Eli Lilly And Company | Novel polymorphic crystalline form of dibenzopyranone |
| US4195078A (en) * | 1979-03-09 | 1980-03-25 | Eli Lilly And Company | Nabilone granulation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3507885A (en) * | 1966-03-25 | 1970-04-21 | Hoffmann La Roche | 3-alkyl-6h-dibenzo(b,d)pyrans |
-
1974
- 1974-09-20 IE IE1949/74A patent/IE39678B1/xx unknown
- 1974-09-23 ZA ZA00746029A patent/ZA746029B/xx unknown
- 1974-09-25 NL NL7412682A patent/NL7412682A/xx not_active Application Discontinuation
- 1974-09-27 IL IL45742A patent/IL45742A/xx unknown
- 1974-09-27 PH PH16343A patent/PH11719A/en unknown
- 1974-10-01 CA CA210,510A patent/CA1028715A/en not_active Expired
- 1974-10-05 ES ES431672A patent/ES431672A1/es not_active Expired
- 1974-10-14 SE SE7412921A patent/SE407062B/xx unknown
- 1974-10-17 SU SU742069769A patent/SU611591A3/ru active
- 1974-10-21 DE DE2449927A patent/DE2449927C2/de not_active Expired
- 1974-10-24 AT AT856674A patent/AT335453B/de not_active IP Right Cessation
- 1974-10-28 YU YU02878/74A patent/YU287874A/xx unknown
- 1974-10-31 PL PL1974175276A patent/PL94119B1/pl unknown
- 1974-10-31 FR FR7436368A patent/FR2249665B1/fr not_active Expired
- 1974-10-31 BE BE150088A patent/BE821720A/xx not_active IP Right Cessation
- 1974-11-04 DD DD182141A patent/DD115660A5/xx unknown
- 1974-11-04 DK DK573374AA patent/DK136720B/da not_active IP Right Cessation
- 1974-11-04 GB GB47516/74A patent/GB1487635A/en not_active Expired
- 1974-11-04 HU HUEI574A patent/HU167751B/hu unknown
- 1974-11-04 CS CS7516A patent/CS174793B2/cs unknown
- 1974-11-05 RO RO7480429A patent/RO71769A/ro unknown
- 1974-11-05 BG BG7428123A patent/BG27088A3/xx unknown
- 1974-11-05 AR AR256414A patent/AR202670A1/es active
- 1974-11-05 JP JP49127923A patent/JPS5943463B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7412682A (nl) | 1975-05-07 |
| PH11719A (en) | 1978-05-30 |
| GB1487635A (en) | 1977-10-05 |
| FR2249665B1 (da) | 1978-07-21 |
| DE2449927A1 (de) | 1975-05-07 |
| FR2249665A1 (da) | 1975-05-30 |
| SE7412921L (da) | 1975-05-06 |
| DK136720B (da) | 1977-11-14 |
| ATA856674A (de) | 1976-07-15 |
| IL45742A0 (en) | 1974-11-29 |
| CS174793B2 (da) | 1977-04-29 |
| DE2449927C2 (de) | 1985-07-04 |
| YU287874A (en) | 1984-04-30 |
| ES431672A1 (es) | 1977-04-16 |
| IE39678L (en) | 1975-05-05 |
| AT335453B (de) | 1977-03-10 |
| RO71769A (ro) | 1981-09-24 |
| AR202670A1 (es) | 1975-06-30 |
| CA1028715A (en) | 1978-03-28 |
| AU7362674A (en) | 1976-04-01 |
| HU167751B (da) | 1975-12-25 |
| BG27088A3 (da) | 1979-08-15 |
| PL94119B1 (da) | 1977-07-30 |
| ZA746029B (en) | 1976-04-28 |
| SU611591A3 (ru) | 1978-06-15 |
| DK136720C (da) | 1978-04-24 |
| JPS5082222A (da) | 1975-07-03 |
| DD115660A5 (da) | 1975-10-12 |
| IE39678B1 (en) | 1978-12-06 |
| BE821720A (fr) | 1975-04-30 |
| SE407062B (sv) | 1979-03-12 |
| IL45742A (en) | 1978-06-15 |
| DK573374A (da) | 1975-07-07 |
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